Versatile electrooxidative amino- and oxyselenation of alkenes

Abstract

Herein, we describe a general and eco-friendly electrochemical methodology for amino- and oxyselenation of alkenes under transition-metal catalyst- and additional-oxidant-free conditions. This electrocatalytic difunctionalisation reaction exhibits excellent chemoselectivity, ample substrate scope, and high functional group tolerance. To our delight, the selenation products (118 examples, up to 99% yield) were constructed from various alkenes including the challenging 1-aryl-1,3-dienes, unactivated aliphatic alkenes, and various N- or O-centered nucleophiles. Preliminary mechanistic studies were conducted. The practical utility of this protocol is highlighted by the gram-scale synthesis and late-stage modification of bioactive molecules.